# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_database_code_depnum_ccdc_archive 'CCDC 1413403'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O3 S'
_chemical_formula_sum            'C15 H14 O3 S'
_chemical_formula_weight         274.32
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4884(5)
_cell_length_b                   11.4294(9)
_cell_length_c                   19.5736(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1227.83(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9202
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13801
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.46
_reflns_number_total             2821
_reflns_number_gt                2504
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_number_reflns         2821
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1843(4) 0.79535(17) 0.70120(10) 0.0172(4) Uani 1 1 d . . .
H1 H 0.0285 0.7851 0.6754 0.021 Uiso 1 1 calc R . .
O1 O 0.2110(3) 0.91475(11) 0.72092(7) 0.0189(3) Uani 1 1 d . . .
H1' H 0.0743 0.9422 0.7316 0.028 Uiso 1 1 calc R . .
C2 C 0.1934(4) 0.70687(16) 0.76210(9) 0.0162(4) Uani 1 1 d . . .
H2 H 0.0259 0.6768 0.7718 0.019 Uiso 1 1 calc R . .
S1 S 0.30846(10) 0.78441(4) 0.83573(2) 0.01794(13) Uani 1 1 d . . .
O2 O 0.5774(3) 0.80157(12) 0.82539(7) 0.0232(3) Uani 1 1 d . . .
C3 C 0.3615(4) 0.60415(17) 0.74055(10) 0.0164(4) Uani 1 1 d . . .
H3 H 0.4800 0.5844 0.7776 0.020 Uiso 1 1 calc R . .
O3 O 0.2097(3) 0.50524(12) 0.72424(8) 0.0223(3) Uani 1 1 d . . .
H3' H 0.2957 0.4517 0.7075 0.033 Uiso 1 1 calc R . .
C3A C 0.4908(4) 0.65135(17) 0.67841(10) 0.0170(4) Uani 1 1 d . . .
C4 C 0.6842(4) 0.60078(17) 0.64338(10) 0.0186(4) Uani 1 1 d . . .
H4 H 0.7523 0.5288 0.6584 0.022 Uiso 1 1 calc R . .
C5 C 0.7758(4) 0.65691(17) 0.58636(10) 0.0202(4) Uani 1 1 d . . .
H5 H 0.9056 0.6223 0.5614 0.024 Uiso 1 1 calc R . .
C6 C 0.6799(4) 0.76370(17) 0.56512(10) 0.0219(4) Uani 1 1 d . . .
H6 H 0.7449 0.8015 0.5259 0.026 Uiso 1 1 calc R . .
C7 C 0.4899(4) 0.81524(18) 0.60087(10) 0.0215(5) Uani 1 1 d . . .
H7 H 0.4257 0.8886 0.5868 0.026 Uiso 1 1 calc R . .
C7A C 0.3951(4) 0.75807(16) 0.65744(10) 0.0177(4) Uani 1 1 d . . .
C8 C 0.2781(4) 0.67403(16) 0.90065(10) 0.0180(4) Uani 1 1 d . . .
C9 C 0.4598(4) 0.67244(18) 0.94993(10) 0.0217(4) Uani 1 1 d . . .
H9 H 0.6032 0.7179 0.9441 0.026 Uiso 1 1 calc R . .
C10 C 0.4299(4) 0.60362(19) 1.00791(11) 0.0244(5) Uani 1 1 d . . .
H10 H 0.5532 0.6021 1.0420 0.029 Uiso 1 1 calc R . .
C11 C 0.2208(4) 0.53732(17) 1.01615(11) 0.0218(5) Uani 1 1 d . . .
H11 H 0.1994 0.4913 1.0561 0.026 Uiso 1 1 calc R . .
C12 C 0.0436(4) 0.5383(2) 0.96613(11) 0.0260(5) Uani 1 1 d . . .
H12 H -0.0977 0.4911 0.9714 0.031 Uiso 1 1 calc R . .
C13 C 0.0691(4) 0.60728(19) 0.90826(11) 0.0244(5) Uani 1 1 d . . .
H13 H -0.0548 0.6087 0.8744 0.029 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.426(2) . ?
C1 C7A 1.501(3) . ?
C1 C2 1.564(3) . ?
C1 H1 1.0000 . ?
O1 H1' 0.8400 . ?
C2 C3 1.552(3) . ?
C2 S1 1.8060(19) . ?
C2 H2 1.0000 . ?
S1 O2 1.5030(16) . ?
S1 C8 1.7983(19) . ?
C3 O3 1.440(2) . ?
C3 C3A 1.508(3) . ?
C3 H3 1.0000 . ?
O3 H3' 0.8400 . ?
C3A C4 1.389(3) . ?
C3A C7A 1.390(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C7A 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.386(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C7A 110.29(17) . . ?
O1 C1 C2 114.16(15) . . ?
C7A C1 C2 103.10(16) . . ?
O1 C1 H1 109.7 . . ?
C7A C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C1 O1 H1' 109.5 . . ?
C3 C2 C1 107.52(15) . . ?
C3 C2 S1 112.35(14) . . ?
C1 C2 S1 107.58(13) . . ?
C3 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
S1 C2 H2 109.8 . . ?
O2 S1 C8 106.12(9) . . ?
O2 S1 C2 107.46(9) . . ?
C8 S1 C2 100.79(9) . . ?
O3 C3 C3A 111.99(16) . . ?
O3 C3 C2 108.06(16) . . ?
C3A C3 C2 103.21(15) . . ?
O3 C3 H3 111.1 . . ?
C3A C3 H3 111.1 . . ?
C2 C3 H3 111.1 . . ?
C3 O3 H3' 109.5 . . ?
C4 C3A C7A 120.52(19) . . ?
C4 C3A C3 127.51(18) . . ?
C7A C3A C3 111.97(17) . . ?
C5 C4 C3A 118.91(19) . . ?
C5 C4 H4 120.5 . . ?
C3A C4 H4 120.5 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C7A 118.99(19) . . ?
C6 C7 H7 120.5 . . ?
C7A C7 H7 120.5 . . ?
C7 C7A C3A 120.49(19) . . ?
C7 C7A C1 127.65(18) . . ?
C3A C7A C1 111.82(17) . . ?
C13 C8 C9 120.87(18) . . ?
C13 C8 S1 122.60(16) . . ?
C9 C8 S1 115.71(16) . . ?
C8 C9 C10 119.3(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.81(19) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.0(2) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -134.82(17) . . . . ?
C7A C1 C2 C3 -15.2(2) . . . . ?
O1 C1 C2 S1 -13.6(2) . . . . ?
C7A C1 C2 S1 106.04(15) . . . . ?
C3 C2 S1 O2 43.86(15) . . . . ?
C1 C2 S1 O2 -74.28(15) . . . . ?
C3 C2 S1 C8 -67.01(15) . . . . ?
C1 C2 S1 C8 174.84(14) . . . . ?
C1 C2 C3 O3 -104.49(18) . . . . ?
S1 C2 C3 O3 137.33(14) . . . . ?
C1 C2 C3 C3A 14.3(2) . . . . ?
S1 C2 C3 C3A -103.92(15) . . . . ?
O3 C3 C3A C4 -72.5(2) . . . . ?
C2 C3 C3A C4 171.56(19) . . . . ?
O3 C3 C3A C7A 107.92(19) . . . . ?
C2 C3 C3A C7A -8.1(2) . . . . ?
C7A C3A C4 C5 -1.6(3) . . . . ?
C3 C3A C4 C5 178.82(19) . . . . ?
C3A C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C7A -0.9(3) . . . . ?
C6 C7 C7A C3A 0.7(3) . . . . ?
C6 C7 C7A C1 -177.11(19) . . . . ?
C4 C3A C7A C7 0.5(3) . . . . ?
C3 C3A C7A C7 -179.81(18) . . . . ?
C4 C3A C7A C1 178.65(18) . . . . ?
C3 C3A C7A C1 -1.7(2) . . . . ?
O1 C1 C7A C7 -49.2(3) . . . . ?
C2 C1 C7A C7 -171.5(2) . . . . ?
O1 C1 C7A C3A 132.84(17) . . . . ?
C2 C1 C7A C3A 10.6(2) . . . . ?
O2 S1 C8 C13 -157.91(17) . . . . ?
C2 S1 C8 C13 -46.00(19) . . . . ?
O2 S1 C8 C9 32.36(18) . . . . ?
C2 S1 C8 C9 144.27(16) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
S1 C8 C9 C10 169.34(16) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
S1 C8 C13 C12 -169.25(17) . . . . ?
C11 C12 C13 C8 1.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.060
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17
_database_code_depnum_ccdc_archive 'CCDC 1413404'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O3 S'
_chemical_formula_sum            'C15 H14 O3 S'
_chemical_formula_weight         274.32
_chemical_absolute_configuration ad


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.292(2)
_cell_length_b                   11.750(3)
_cell_length_c                   14.698(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1259.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prisms
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_T_max  0.9503
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13537
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         28.65
_reflns_number_total             2915
_reflns_number_gt                2303
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1060P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(14)
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4882(5) 0.5877(3) 0.2782(2) 0.0222(7) Uani 1 1 d . . .
H1 H 0.3536 0.5714 0.2793 0.027 Uiso 1 1 calc R . .
O1 O 0.5817(4) 0.49879(18) 0.23090(16) 0.0283(6) Uani 1 1 d . . .
H1' H 0.6897 0.5193 0.2197 0.043 Uiso 1 1 calc R . .
C2 C 0.5222(4) 0.7049(3) 0.2352(2) 0.0207(7) Uani 1 1 d . . .
H2 H 0.5616 0.6971 0.1703 0.025 Uiso 1 1 calc R . .
O2 O 0.3571(3) 0.7670(2) 0.24160(16) 0.0245(5) Uani 1 1 d . . .
H2' H 0.3798 0.8369 0.2377 0.037 Uiso 1 1 calc R . .
C3 C 0.6743(4) 0.7598(3) 0.2927(2) 0.0203(7) Uani 1 1 d . . .
H3 H 0.6526 0.8435 0.2992 0.024 Uiso 1 1 calc R . .
S1 S 0.90341(11) 0.73261(7) 0.24667(6) 0.0233(2) Uani 1 1 d . . .
O3 O 0.9041(4) 0.6092(2) 0.22052(17) 0.0299(6) Uani 1 1 d . . .
C3A C 0.6586(5) 0.7015(3) 0.3830(2) 0.0212(7) Uani 1 1 d . . .
C4 C 0.7320(5) 0.7318(3) 0.4651(2) 0.0252(7) Uani 1 1 d . . .
H4 H 0.8011 0.8000 0.4710 0.030 Uiso 1 1 calc R . .
C5 C 0.7043(5) 0.6618(3) 0.5395(2) 0.0285(8) Uani 1 1 d . . .
H5 H 0.7522 0.6827 0.5972 0.034 Uiso 1 1 calc R . .
C6 C 0.6068(6) 0.5615(3) 0.5298(2) 0.0289(8) Uani 1 1 d . . .
H6 H 0.5893 0.5135 0.5811 0.035 Uiso 1 1 calc R . .
C7 C 0.5349(5) 0.5302(3) 0.4471(2) 0.0275(8) Uani 1 1 d . . .
H7 H 0.4707 0.4604 0.4406 0.033 Uiso 1 1 calc R . .
C7A C 0.5575(5) 0.6020(3) 0.3736(2) 0.0212(7) Uani 1 1 d . . .
C8 C 0.8895(5) 0.8099(3) 0.1434(2) 0.0225(7) Uani 1 1 d . . .
C9 C 0.9464(6) 0.9222(3) 0.1451(3) 0.0302(8) Uani 1 1 d . . .
H9 H 0.9839 0.9569 0.2004 0.036 Uiso 1 1 calc R . .
C10 C 0.9477(6) 0.9828(3) 0.0647(3) 0.0367(9) Uani 1 1 d . . .
H10 H 0.9865 1.0600 0.0648 0.044 Uiso 1 1 calc R . .
C11 C 0.8938(6) 0.9330(3) -0.0151(3) 0.0340(9) Uani 1 1 d . . .
H11 H 0.8953 0.9757 -0.0700 0.041 Uiso 1 1 calc R . .
C12 C 0.8369(5) 0.8202(4) -0.0159(3) 0.0322(9) Uani 1 1 d . . .
H12 H 0.7990 0.7857 -0.0713 0.039 Uiso 1 1 calc R . .
C13 C 0.8357(5) 0.7589(3) 0.0633(2) 0.0267(8) Uani 1 1 d . . .
H13 H 0.7979 0.6815 0.0631 0.032 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.428(4) . ?
C1 C7A 1.500(4) . ?
C1 C2 1.536(4) . ?
C1 H1 1.0000 . ?
O1 H1' 0.8400 . ?
C2 O2 1.411(4) . ?
C2 C3 1.536(4) . ?
C2 H2 1.0000 . ?
O2 H2' 0.8400 . ?
C3 C3A 1.499(4) . ?
C3 S1 1.830(3) . ?
C3 H3 1.0000 . ?
S1 O3 1.500(2) . ?
S1 C8 1.771(3) . ?
C3A C4 1.367(5) . ?
C3A C7A 1.389(5) . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(5) . ?
C6 H6 0.9500 . ?
C7 C7A 1.381(5) . ?
C7 H7 0.9500 . ?
C8 C13 1.378(5) . ?
C8 C9 1.384(5) . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C7A 112.1(3) . . ?
O1 C1 C2 112.2(3) . . ?
C7A C1 C2 103.3(3) . . ?
O1 C1 H1 109.7 . . ?
C7A C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C1 O1 H1' 109.5 . . ?
O2 C2 C1 107.4(3) . . ?
O2 C2 C3 111.2(3) . . ?
C1 C2 C3 105.5(3) . . ?
O2 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
C2 O2 H2' 109.5 . . ?
C3A C3 C2 103.9(3) . . ?
C3A C3 S1 108.5(2) . . ?
C2 C3 S1 112.5(2) . . ?
C3A C3 H3 110.6 . . ?
C2 C3 H3 110.6 . . ?
S1 C3 H3 110.6 . . ?
O3 S1 C8 106.03(15) . . ?
O3 S1 C3 105.46(16) . . ?
C8 S1 C3 100.06(15) . . ?
C4 C3A C7A 121.0(3) . . ?
C4 C3A C3 129.3(3) . . ?
C7A C3A C3 109.7(3) . . ?
C3A C4 C5 119.0(3) . . ?
C3A C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C7A 119.0(3) . . ?
C6 C7 H7 120.5 . . ?
C7A C7 H7 120.5 . . ?
C7 C7A C3A 119.9(3) . . ?
C7 C7A C1 128.6(3) . . ?
C3A C7A C1 111.5(3) . . ?
C13 C8 C9 121.0(3) . . ?
C13 C8 S1 121.7(3) . . ?
C9 C8 S1 117.2(3) . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 143.0(3) . . . . ?
C7A C1 C2 O2 -96.1(3) . . . . ?
O1 C1 C2 C3 -98.3(3) . . . . ?
C7A C1 C2 C3 22.6(3) . . . . ?
O2 C2 C3 C3A 91.6(3) . . . . ?
C1 C2 C3 C3A -24.5(3) . . . . ?
O2 C2 C3 S1 -151.3(2) . . . . ?
C1 C2 C3 S1 92.6(3) . . . . ?
C3A C3 S1 O3 70.9(2) . . . . ?
C2 C3 S1 O3 -43.4(3) . . . . ?
C3A C3 S1 C8 -179.2(2) . . . . ?
C2 C3 S1 C8 66.4(2) . . . . ?
C2 C3 C3A C4 -164.9(3) . . . . ?
S1 C3 C3A C4 75.3(4) . . . . ?
C2 C3 C3A C7A 17.4(4) . . . . ?
S1 C3 C3A C7A -102.5(3) . . . . ?
C7A C3A C4 C5 -0.1(5) . . . . ?
C3 C3A C4 C5 -177.6(3) . . . . ?
C3A C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C5 C6 C7 C7A -1.5(6) . . . . ?
C6 C7 C7A C3A 2.8(5) . . . . ?
C6 C7 C7A C1 -178.4(4) . . . . ?
C4 C3A C7A C7 -2.1(5) . . . . ?
C3 C3A C7A C7 175.9(3) . . . . ?
C4 C3A C7A C1 178.9(3) . . . . ?
C3 C3A C7A C1 -3.1(4) . . . . ?
O1 C1 C7A C7 -70.4(5) . . . . ?
C2 C1 C7A C7 168.6(4) . . . . ?
O1 C1 C7A C3A 108.5(3) . . . . ?
C2 C1 C7A C3A -12.5(4) . . . . ?
O3 S1 C8 C13 16.7(3) . . . . ?
C3 S1 C8 C13 -92.7(3) . . . . ?
O3 S1 C8 C9 -159.2(3) . . . . ?
C3 S1 C8 C9 91.4(3) . . . . ?
C13 C8 C9 C10 0.2(6) . . . . ?
S1 C8 C9 C10 176.2(3) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 0.5(6) . . . . ?
C9 C8 C13 C12 -0.5(6) . . . . ?
S1 C8 C13 C12 -176.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.65
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.085
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20b
_database_code_depnum_ccdc_archive 'CCDC 1413405'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 O3 S1'
_chemical_formula_sum            'C12 H12 O3 S1'
_chemical_formula_weight         236.3
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.108(3)
_cell_length_b                   11.284(4)
_cell_length_c                   24.513(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2242.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P3 diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4569
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         32.56
_reflns_number_total             4569
_reflns_number_gt                3069
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens P3/V2000'
_computing_cell_refinement       'Siemens P3/V2000'
_computing_data_reduction        'Siemens P3/V2000'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_number_reflns         4569
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3836(3) 0.0711(3) 0.95099(11) 0.0377(6) Uani 1 1 d . . .
H1 H 0.3917 -0.0146 0.9451 0.045 Uiso 1 1 calc R . .
O1 O 0.3018(3) 0.0848(2) 1.00116(9) 0.0536(6) Uani 1 1 d . . .
H1A H 0.2697 0.1534 1.0042 0.080 Uiso 1 1 calc R . .
C2 C 0.5607(3) 0.1161(2) 0.95271(11) 0.0318(6) Uani 1 1 d . . .
H2 H 0.6229 0.0667 0.9783 0.038 Uiso 1 1 calc R . .
O2 O 0.5738(3) 0.23662(17) 0.97000(7) 0.0397(5) Uani 1 1 d . . .
H2A H 0.5120 0.2780 0.9516 0.060 Uiso 1 1 calc R . .
C3 C 0.6340(3) 0.0995(2) 0.89625(11) 0.0317(5) Uani 1 1 d . . .
S1 S 0.85064(9) 0.07942(7) 0.89182(3) 0.03573(17) Uani 1 1 d . . .
O3 O 0.8911(3) 0.07017(19) 0.83208(8) 0.0459(5) Uani 1 1 d . . .
C4 C 0.5435(4) 0.1131(3) 0.85138(11) 0.0361(6) Uani 1 1 d . . .
H4 H 0.5934 0.1086 0.8173 0.043 Uiso 1 1 calc R . .
C5 C 0.3667(4) 0.1350(3) 0.85535(13) 0.0416(7) Uani 1 1 d . . .
H5 H 0.3073 0.1602 0.8251 0.050 Uiso 1 1 calc R . .
C6 C 0.2917(4) 0.1182(3) 0.90309(13) 0.0413(7) Uani 1 1 d . . .
H6 H 0.1803 0.1362 0.9065 0.050 Uiso 1 1 calc R . .
C7 C 0.8657(3) -0.0681(3) 0.91845(11) 0.0380(6) Uani 1 1 d . . .
C8 C 0.8200(5) -0.1629(3) 0.88652(15) 0.0617(10) Uani 1 1 d . . .
H8 H 0.7775 -0.1506 0.8517 0.074 Uiso 1 1 calc R . .
C9 C 0.8377(6) -0.2758(3) 0.90643(17) 0.0736(12) Uani 1 1 d . . .
H9 H 0.8068 -0.3404 0.8852 0.088 Uiso 1 1 calc R . .
C10 C 0.9008(6) -0.2932(4) 0.95755(17) 0.0758(13) Uani 1 1 d . . .
H10 H 0.9120 -0.3699 0.9709 0.091 Uiso 1 1 calc R . .
C11 C 0.9468(6) -0.2007(4) 0.98880(16) 0.0814(14) Uani 1 1 d . . .
H11 H 0.9889 -0.2141 1.0236 0.098 Uiso 1 1 calc R . .
C12 C 0.9320(5) -0.0848(4) 0.96947(13) 0.0584(9) Uani 1 1 d . . .
H12 H 0.9660 -0.0207 0.9905 0.070 Uiso 1 1 calc R . .
C1A C 0.4600(4) 0.1398(3) 1.22957(12) 0.0444(7) Uani 1 1 d . . .
H1A1 H 0.4127 0.1093 1.2636 0.053 Uiso 1 1 calc R . .
O1A O 0.5192(4) 0.2566(2) 1.23928(9) 0.0624(7) Uani 1 1 d . . .
H1A2 H 0.4810 0.3018 1.2163 0.094 Uiso 1 1 calc R . .
C2A C 0.5991(3) 0.0574(3) 1.21210(10) 0.0348(6) Uani 1 1 d . . .
H2A1 H 0.5567 -0.0239 1.2131 0.042 Uiso 1 1 calc R . .
O2A O 0.7374(2) 0.0629(2) 1.24681(8) 0.0441(5) Uani 1 1 d . . .
H2A2 H 0.7161 0.0295 1.2757 0.066 Uiso 1 1 calc R . .
C3A C 0.6508(4) 0.0834(2) 1.15450(10) 0.0334(5) Uani 1 1 d . . .
S1A S 0.86324(10) 0.07313(7) 1.13764(3) 0.03917(18) Uani 1 1 d . . .
O3A O 0.8742(3) 0.08984(19) 1.07694(9) 0.0535(6) Uani 1 1 d . . .
C4A C 0.5377(4) 0.1120(3) 1.11720(12) 0.0407(7) Uani 1 1 d . . .
H4A H 0.5673 0.1232 1.0809 0.049 Uiso 1 1 calc R . .
C5A C 0.3662(4) 0.1252(3) 1.13467(14) 0.0451(7) Uani 1 1 d . . .
H5A H 0.2825 0.1247 1.1087 0.054 Uiso 1 1 calc R . .
C6A C 0.3285(4) 0.1376(3) 1.18650(13) 0.0491(8) Uani 1 1 d . . .
H6A H 0.2185 0.1453 1.1967 0.059 Uiso 1 1 calc R . .
C7A C 0.8842(4) -0.0818(3) 1.15247(12) 0.0416(7) Uani 1 1 d . . .
C8A C 0.7840(5) -0.1647(3) 1.12765(16) 0.0594(10) Uani 1 1 d . . .
H8A H 0.7072 -0.1415 1.1016 0.071 Uiso 1 1 calc R . .
C9A C 0.7993(6) -0.2831(3) 1.14214(19) 0.0719(12) Uani 1 1 d . . .
H9A H 0.7324 -0.3402 1.1261 0.086 Uiso 1 1 calc R . .
C10A C 0.9153(6) -0.3152(3) 1.18078(18) 0.0756(14) Uani 1 1 d . . .
H10A H 0.9251 -0.3944 1.1907 0.091 Uiso 1 1 calc R . .
C11A C 1.0151(6) -0.2336(3) 1.20462(15) 0.0685(12) Uani 1 1 d . . .
H11A H 1.0925 -0.2570 1.2305 0.082 Uiso 1 1 calc R . .
C12A C 1.0009(5) -0.1154(3) 1.19017(15) 0.0545(9) Uani 1 1 d . . .
H12A H 1.0698 -0.0590 1.2059 0.065 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.406(3) . ?
C1 C6 1.489(4) . ?
C1 C2 1.524(4) . ?
C1 H1 0.9800 . ?
O1 H1A 0.8200 . ?
C2 O2 1.428(3) . ?
C2 C3 1.518(4) . ?
C2 H2 0.9800 . ?
O2 H2A 0.8200 . ?
C3 C4 1.331(4) . ?
C3 S1 1.775(3) . ?
S1 O3 1.504(2) . ?
S1 C7 1.792(3) . ?
C4 C5 1.457(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.332(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.374(4) . ?
C7 C8 1.377(5) . ?
C8 C9 1.372(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.348(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C1A O1A 1.424(4) . ?
C1A C6A 1.501(4) . ?
C1A C2A 1.523(4) . ?
C1A H1A1 0.9800 . ?
O1A H1A2 0.8200 . ?
C2A O2A 1.409(3) . ?
C2A C3A 1.502(4) . ?
C2A H2A1 0.9800 . ?
O2A H2A2 0.8200 . ?
C3A C4A 1.334(4) . ?
C3A S1A 1.775(3) . ?
S1A O3A 1.503(2) . ?
S1A C7A 1.794(3) . ?
C4A C5A 1.463(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.314(5) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C12A 1.376(5) . ?
C7A C8A 1.380(5) . ?
C8A C9A 1.388(5) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.383(6) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.358(6) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.385(5) . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 114.5(2) . . ?
O1 C1 C2 112.6(2) . . ?
C6 C1 C2 112.0(2) . . ?
O1 C1 H1 105.6 . . ?
C6 C1 H1 105.6 . . ?
C2 C1 H1 105.6 . . ?
C1 O1 H1A 109.5 . . ?
O2 C2 C3 111.0(2) . . ?
O2 C2 C1 113.3(2) . . ?
C3 C2 C1 107.6(2) . . ?
O2 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C2 O2 H2A 109.5 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 S1 120.6(2) . . ?
C2 C3 S1 117.32(19) . . ?
O3 S1 C3 106.51(13) . . ?
O3 S1 C7 105.98(13) . . ?
C3 S1 C7 99.44(13) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C12 C7 C8 121.0(3) . . ?
C12 C7 S1 119.1(3) . . ?
C8 C7 S1 119.8(2) . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 118.1(4) . . ?
C7 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
O1A C1A C6A 111.8(3) . . ?
O1A C1A C2A 111.3(3) . . ?
C6A C1A C2A 108.6(2) . . ?
O1A C1A H1A1 108.4 . . ?
C6A C1A H1A1 108.4 . . ?
C2A C1A H1A1 108.4 . . ?
C1A O1A H1A2 109.5 . . ?
O2A C2A C3A 109.7(2) . . ?
O2A C2A C1A 113.1(2) . . ?
C3A C2A C1A 110.6(2) . . ?
O2A C2A H2A1 107.7 . . ?
C3A C2A H2A1 107.7 . . ?
C1A C2A H2A1 107.7 . . ?
C2A O2A H2A2 109.5 . . ?
C4A C3A C2A 120.0(3) . . ?
C4A C3A S1A 121.5(2) . . ?
C2A C3A S1A 118.5(2) . . ?
O3A S1A C3A 106.23(14) . . ?
O3A S1A C7A 108.50(14) . . ?
C3A S1A C7A 96.24(14) . . ?
C3A C4A C5A 118.5(3) . . ?
C3A C4A H4A 120.7 . . ?
C5A C4A H4A 120.7 . . ?
C6A C5A C4A 121.0(3) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
C5A C6A C1A 121.1(3) . . ?
C5A C6A H6A 119.4 . . ?
C1A C6A H6A 119.4 . . ?
C12A C7A C8A 121.0(3) . . ?
C12A C7A S1A 118.0(3) . . ?
C8A C7A S1A 121.0(3) . . ?
C7A C8A C9A 119.1(4) . . ?
C7A C8A H8A 120.4 . . ?
C9A C8A H8A 120.4 . . ?
C10A C9A C8A 119.2(4) . . ?
C10A C9A H9A 120.4 . . ?
C8A C9A H9A 120.4 . . ?
C11A C10A C9A 121.5(4) . . ?
C11A C10A H10A 119.2 . . ?
C9A C10A H10A 119.2 . . ?
C10A C11A C12A 119.5(4) . . ?
C10A C11A H11A 120.2 . . ?
C12A C11A H11A 120.2 . . ?
C7A C12A C11A 119.6(4) . . ?
C7A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -55.5(3) . . . . ?
C6 C1 C2 O2 75.2(3) . . . . ?
O1 C1 C2 C3 -178.6(2) . . . . ?
C6 C1 C2 C3 -47.9(3) . . . . ?
O2 C2 C3 C4 -89.2(3) . . . . ?
C1 C2 C3 C4 35.3(3) . . . . ?
O2 C2 C3 S1 83.2(2) . . . . ?
C1 C2 C3 S1 -152.29(19) . . . . ?
C4 C3 S1 O3 -5.3(3) . . . . ?
C2 C3 S1 O3 -177.80(19) . . . . ?
C4 C3 S1 C7 -115.2(2) . . . . ?
C2 C3 S1 C7 72.3(2) . . . . ?
C2 C3 C4 C5 -5.1(4) . . . . ?
S1 C3 C4 C5 -177.2(2) . . . . ?
C3 C4 C5 C6 -13.0(5) . . . . ?
C4 C5 C6 C1 -3.6(5) . . . . ?
O1 C1 C6 C5 165.3(3) . . . . ?
C2 C1 C6 C5 35.6(4) . . . . ?
O3 S1 C7 C12 141.5(3) . . . . ?
C3 S1 C7 C12 -108.2(3) . . . . ?
O3 S1 C7 C8 -34.8(3) . . . . ?
C3 S1 C7 C8 75.6(3) . . . . ?
C12 C7 C8 C9 1.4(6) . . . . ?
S1 C7 C8 C9 177.6(4) . . . . ?
C7 C8 C9 C10 -0.2(7) . . . . ?
C8 C9 C10 C11 -0.3(8) . . . . ?
C9 C10 C11 C12 -0.4(8) . . . . ?
C8 C7 C12 C11 -2.1(6) . . . . ?
S1 C7 C12 C11 -178.2(3) . . . . ?
C10 C11 C12 C7 1.5(7) . . . . ?
O1A C1A C2A O2A 49.9(3) . . . . ?
C6A C1A C2A O2A 173.3(2) . . . . ?
O1A C1A C2A C3A -73.6(3) . . . . ?
C6A C1A C2A C3A 49.9(3) . . . . ?
O2A C2A C3A C4A -163.4(3) . . . . ?
C1A C2A C3A C4A -38.0(4) . . . . ?
O2A C2A C3A S1A 17.4(3) . . . . ?
C1A C2A C3A S1A 142.9(2) . . . . ?
C4A C3A S1A O3A -5.5(3) . . . . ?
C2A C3A S1A O3A 173.7(2) . . . . ?
C4A C3A S1A C7A -116.8(3) . . . . ?
C2A C3A S1A C7A 62.3(2) . . . . ?
C2A C3A C4A C5A 4.2(4) . . . . ?
S1A C3A C4A C5A -176.7(2) . . . . ?
C3A C4A C5A C6A 16.4(5) . . . . ?
C4A C5A C6A C1A 0.5(5) . . . . ?
O1A C1A C6A C5A 89.3(4) . . . . ?
C2A C1A C6A C5A -33.9(4) . . . . ?
O3A S1A C7A C12A 127.6(3) . . . . ?
C3A S1A C7A C12A -123.0(3) . . . . ?
O3A S1A C7A C8A -53.8(3) . . . . ?
C3A S1A C7A C8A 55.7(3) . . . . ?
C12A C7A C8A C9A 1.5(5) . . . . ?
S1A C7A C8A C9A -177.1(3) . . . . ?
C7A C8A C9A C10A -0.4(6) . . . . ?
C8A C9A C10A C11A -0.4(6) . . . . ?
C9A C10A C11A C12A 0.1(6) . . . . ?
C8A C7A C12A C11A -1.8(5) . . . . ?
S1A C7A C12A C11A 176.9(3) . . . . ?
C10A C11A C12A C7A 0.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        32.56
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.050
